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13. 1929 Mercedes-Benz 38/250 SSK

Price: $7.4 million Auction: Bonhams Goodwood, UK 2004

This German roadster was built between 1928 and 1932. Classically beautiful but it was also a beast on the track, the Super Sport Kurz, German for "Super Sport Short"; got its name since it boasted a shorter wheelbase than the previous Mercedes-Benz SS. The list of victories at legendary Grand Prix's around the world is quite extensive, among them is the 1931 Mille Miglia. Notabaly, the SSK was the last car designed for Mercedes-Benz by Ferdinand Porsche before he left to found his own car company.

Supercharged with nearly 300 horsepower and top speed of 120, this was also the fastest car of its day. Aside from this famously expensive one sold at Bonhams, Ralph Lauren is also a proud owner of the prestigious SSK, his has one Best in Show at Pebble Beach.